2-debromostevensine - Compound Card

2-debromostevensine

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2-debromostevensine

Structure
Zoomed Structure
  • Family: Animalia - Dictyonellidae
  • Kingdom: Animalia
  • Class: Alkaloid
Canonical Smiles Brc1c[nH]c2c1C(=CCNC2=O)c1c[nH]c(=[NH2+])[nH]1
InChI InChI=1S/C11H10BrN5O/c12-6-3-15-9-8(6)5(1-2-14-10(9)18)7-4-16-11(13)17-7/h1,3-4,15H,2H2,(H,14,18)(H3,13,16,17)/p+1
InChIKey ZQPORTJXDDLMGI-UHFFFAOYSA-O
Formula C11H11BrN5O+
HBA 1
HBD 5
MW 309.15
Rotatable Bonds 1
TPSA 102.06
LogP -0.73
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 18
Formal Charge 1
Fraction CSP3 0.09
Exact Mass 308.01
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Stylissa species Dictyonellidae Animalia 237127

Showing of synonyms

  • Fouad MA, Debbab A, et al. (2012). New bioactive alkaloids from the marine sponge Stylissa sp.. Tetrahedron,2012,68,10176-10179. [View]
Pubchem: 21775271

No compound-protein relationship available.

Structure

SMILES: c1c[nH]c(c12)C(=O)NCC=C2c3c[nH]c(=[NH2+])[nH]3

Level: 1

Mol. Weight: 309.15 g/mol

Structure

SMILES: c1c[nH]c(c12)C(=O)NCC=C2

Level: 0

Mol. Weight: 309.15 g/mol

Structure

SMILES: [NH2+]=c1[nH]cc[nH]1

Level: 0

Mol. Weight: 309.15 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.41
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.61
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
13.17
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.51
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.38
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.64
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.6
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.03
Rat (Acute)
2.19
Rat (Chronic Oral)
2.51
Fathead Minnow
5.57
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
515.23
Hydration Free Energy
-10.65
Log(D) at pH=7.4
0.59
Log(P)
-0.8
Log S
-2.66
Log(Vapor Pressure)
-9.34
Melting Point
401.27
pKa Acid
8.8
pKa Basic
4.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.9071
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.9071
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9036
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9036
Glucanase Q7LHI2 Q7LHI2_PHACH Phanerodontia chrysosporium 3 0.8960
Glucanase Q7LHI2 Q7LHI2_PHACH Phanerodontia chrysosporium 3 0.8960
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8942
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8942
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8906
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8906
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8655
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8655
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8625
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8625
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.8599
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.8599
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8533
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8533
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8473
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8473
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8180
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8180
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8129
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8129
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 3 0.8084
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 3 0.8084
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 3 0.8061
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 3 0.8061
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8056
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8056
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8036
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8036
Purine nucleoside phosphorylase, putative A2E7Y6 A2E7Y6_TRIVA Trichomonas vaginalis 3 0.7936
Purine nucleoside phosphorylase, putative A2E7Y6 A2E7Y6_TRIVA Trichomonas vaginalis 3 0.7936
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7880
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7880
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7855
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7855
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7817
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7817
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7812
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7812
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7697
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7697
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7643
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7643
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7630
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7630
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7620
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7620
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7614
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7614
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7590
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7590
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7546
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7546
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7546
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7546
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7505
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7505
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7482
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7482
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7469
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7469
Purine nucleoside phosphorylase, putative A2E7Y6 A2E7Y6_TRIVA Trichomonas vaginalis 3 0.7467
Purine nucleoside phosphorylase, putative A2E7Y6 A2E7Y6_TRIVA Trichomonas vaginalis 3 0.7467
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7463
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7463
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7442
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7442
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7425
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7425
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7423
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7423
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.7422
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.7422
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7362
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7362
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7356
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7356
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7353
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7353
Arginine kinase O15992 KARG_ANTJA Anthopleura japonica 2 0.7350
Arginine kinase O15992 KARG_ANTJA Anthopleura japonica 2 0.7350
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7340
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7340
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7339
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7339
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7329
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7329
Purine phosphoribosyltransferase (GpT-1) Q97W95 Q97W95_SACS2 Saccharolobus solfataricus 3 0.7319
Purine phosphoribosyltransferase (GpT-1) Q97W95 Q97W95_SACS2 Saccharolobus solfataricus 3 0.7319
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7280
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7280
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7274
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7274
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7266
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7266
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7263
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7263
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7263
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7263
chitinase B0Y2Y2 B0Y2Y2_ASPFC Aspergillus fumigatus 3 0.7257
chitinase B0Y2Y2 B0Y2Y2_ASPFC Aspergillus fumigatus 3 0.7257
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7204
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7204
3-oxoacyl-[acyl-carrier-protein] synthase 2 P0AAI5 FABF_ECOLI Escherichia coli 3 0.7195
3-oxoacyl-[acyl-carrier-protein] synthase 2 P0AAI5 FABF_ECOLI Escherichia coli 3 0.7195
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7194
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7194
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7189
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7189
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7172
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7172
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7166
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7166
Tyrosine-protein kinase ABL1 P00519 ABL1_HUMAN Homo sapiens 3 0.7166
Tyrosine-protein kinase ABL1 P00519 ABL1_HUMAN Homo sapiens 3 0.7166
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7158
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7158
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7156
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7156
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7150
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7150
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7146
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7146
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7143
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7143
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7141
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7141
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7139
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7139
Purine nucleoside phosphorylase P50389 PNPH_SACS2 Saccharolobus solfataricus 3 0.7125
Purine nucleoside phosphorylase P50389 PNPH_SACS2 Saccharolobus solfataricus 3 0.7125
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7118
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7118
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7104
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7104
DNA (cytosine-5)-methyltransferase 3A O88508 DNM3A_MOUSE Mus musculus 3 0.7102
DNA (cytosine-5)-methyltransferase 3A O88508 DNM3A_MOUSE Mus musculus 3 0.7102
5'-methylthioadenosine nucleosidase / s-adenosylhomocysteine nucleosidase Q8YBL1 Q8YBL1_BRUME Brucella melitensis biotype 1 3 0.7100
5'-methylthioadenosine nucleosidase / s-adenosylhomocysteine nucleosidase Q8YBL1 Q8YBL1_BRUME Brucella melitensis biotype 1 3 0.7100
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7096
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7096
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7095
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7095
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 2 0.7095
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 2 0.7095
Ribonucleoside-diphosphate reductase large chain 1 P21524 RIR1_YEAST Saccharomyces cerevisiae 2 0.7053
Ribonucleoside-diphosphate reductase large chain 1 P21524 RIR1_YEAST Saccharomyces cerevisiae 2 0.7053
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7042
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7042
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7042
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7042
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7041
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7041
Gamma-aminobutyric acid type B receptor subunit 1 Q9UBS5 GABR1_HUMAN Homo sapiens 2 0.7030
Gamma-aminobutyric acid type B receptor subunit 1 Q9UBS5 GABR1_HUMAN Homo sapiens 2 0.7030
Polyamine aminopropyltransferase Q5SK28 SPEE_THET8 Thermus thermophilus 3 0.7015
Polyamine aminopropyltransferase Q5SK28 SPEE_THET8 Thermus thermophilus 3 0.7015
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7013
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7013
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7008
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7008
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7008
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7008
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7004
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7004
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7001
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7001

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